[camurphy519]

I have a few homework problems I am stuck on. I am already struggling with the material and trying to teach myself as much as possible, so any help with these 2 questions would greatly appreciated!

How would you make the following compounds starting with acetylene. If compound cannot be prepared using this method say so.
1. 4-methyl-2-hexyne
2. 5-methyl-2-hexyne

I am using the David Klein Organic Chemistry textbook and I am finding that there are not too many examples like this to guide me and the teacher did do any problems in class, just assigned them.

[discodermolide]

Well what do you know about acetylene (chemical reactions of)?

[camurphy519]

Well, I tried reading my book and then a bunch of other sources, so I think I have just about completely confused myself. But I know acetylene is used in alkylation of terminal alkynes. Since acetylene has 2 terminal protons it can undergo alkylation twice, and that the acetylide ion is used with a primary alkyl halide, otherwise it undergoes elimination.
I haven't quite mastered mechanisms or choosing what halide to use in a reaction so I always second guess myself, and I think since the compounds have substituents it is really just throwing me off.

[discodermolide]

OK, that seems ok.
Now which alkyl halides would you then choose to make your compounds? One is common to both products.